TLDR: AI is changing how buyers experience outreach, but the sellers winning right now aren't the ones who automate the most. They're the ones who know when to be human. This episode breaks down engineered empathy, what RevOps leaders should actually be doing, and why boot camp style skills training is making a comeback.

AI can write the email. It can personalize the subject line, pull your prospect's LinkedIn activity, and generate a follow-up sequence in seconds. But when the conversation goes deeper and when a buyer actually engages, the sellers who close are the ones who can read the room, adjust in real time, and make someone feel like they're talking to another person, not a machine.

Kelly Lewis and Tiffany Jones dig into the concept of engineered empathy, first introduced on the show by sales strategist Brynn Tillman, and why it's exposing a real gap in how GTM orgs are deploying AI right now. They also cover what this means for RevOps career paths, where enablement is headed as tool training gives way to skill development, and why Tiffany is making a major move, going full-time with The Revenue Insiders.

In This Episode:

Why engineered empathy is the biggest AI risk in outbound sales right now
How senior sellers use AI differently than junior reps — and what enablement should do about it
The case for bringing back boot camp style skills training as SDR automation frees up budget
How to think about RevOps and enablement career paths when the tools keep changing
Tiffany's announcement: leaving corporate and joining The Revenue Insiders full-time

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The Real Reason AI Can't Replace Your Best Sellers